


Dark and Dangerous

by Askellie



Category: Undertale (Video Game)
Genre: Blood and Gore, Bondage, Chastity Device, Coercion, Cuckolding, Drugging, Drugs, Dubious Consent, Fisting, Force-Feeding, Forced Orgasm, Fucking Machines, Heavy Drinking, Hypnotism, Injury, M/M, Mind Control, Non-Consensual Somnophilia, Non-Consensual Touching, Orgasm Denial, Overstimulation, Oviposition, Predicament Bondage, Sexual Coercion, Sibling Incest, Tears, Tentacles, Torture, Vibrators, Vore, cum milking
Language: English
Status: In-Progress
Published: 2019-10-01
Updated: 2019-10-22
Packaged: 2020-11-08 18:51:40
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 14
Words: 18,200
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20840327
Author URL: https://archiveofourown.org/users/Askellie/pseuds/Askellie
Summary: [Prompt 14] Edge has admired Black's well trained mutt for some time.----A Darkfic Kinktober Prompts Series





	1. Friends with Benefits (HoneyPuppyMoney)

**Author's Note:**

> [idontevenknowugh](https://archiveofourown.org/users/idontevenknowugh/pseuds/idontevenknowugh) came up with a Dark Fic kink list for October which is everything I want to try and shouldn't be doing but oops here it is anyway. No promises on actually posting every day, but there'll probably be a few of these before the month is up.
> 
> Day 1 Prompt is Mind Control | Hypnotism

When Slim had first passed Stretch the joint, crooked fangs making his sly smile seem more playful than wicked, Stretch had promised himself he’d be careful. Just one or two hits, enough to be a little loose, but not enough to turn into the giddily dull-witted mess he often turned into in the privacy of his own room. 

It was a noble intention that had been utterly forgotten after the third -- fourth?? -- drink Cash had offered him. His brother would never say a bad word about their extended skeleton family, but there had been a look of tight concern in his sockets when Stretch had told him who he was hanging out with this evening. It was an open secret that Cash and Slim were the kind of ‘bad influence’ Blue had been warning him about all his life, but as far as Stretch was concerned, they were the BEST bad influence and he was having a GREAT time.

Contrary to his usual stingy habits, Cash was being unusually generous, as if Stretch’s presence was worthy of a celebration. He was keeping Stretch’s glass topped up, plying him with some kind of sweet cocktail that burned pleasantly on his tongue. Normally he’d be sure Cash was just tricking him into running up a tab, and would expect to find himself presented with a massive bill at the end of the night, but Cash had dismissed his half-serious accusation with a sharp grin and a promise that he wasn’t keeping track.

“He can’t count when he’s high,” Slim told him in an extremely unconfidential whisper, sending the two of them into a snickering fit as the joint changed hands again.

“Fuck off,” Cash grumbled, though without much heat as he took a heavy drag. “S’not like you two chucklefucks could do any better. Besides, ‘least I can still do this.”

With an almost absurdly dramatic flourish, he produced a gold coin seemingly from nowhere. He presented it with a magician’s finesse, spinning it between his thumb and forefinger, before sending it to roll down his knuckles. It somersaulted over each phalange before dexterously being pulled back across the palm to start again from the top in a circuitous dance. It was admittedly kind of impressive, though more so that Cash could keep the coin moving so fluidly while he was half-drunk and high. The ripple of his phalanges was practiced and smooth. He must have put a lot of hours in to mastering it. 

“Coin tricks?” Stretch scoffed. “Dude, you know we can use actual magic, right?”

Cash smirked. “Sure. Like this?”

The coin was still moving over his fingers, but now it was vanishing and reappearing in an impossible journey, jumping from hand to hand, almost impossible to follow except for the glint of gold flashing dazzlingly in the light. Stretch let out a startled laugh, delighted with the absurdity of it.

“Yeah, okay. That’s pretty cool,” he conceded. He flicked a sideways glance at Slim to see if he was also enjoying the show, but oddly Slim’s face was turned aside, deliberately facing the far wall. As stoned as he was, maybe the wall was more interesting. Stretch gave a mental shrug, turning his attention back to the coin. Even if it was a silly party trick rather than a more impressive show of magic, it was hard to tear his gaze away from the coin. There was something profoundly pleasing about it; the smoothness of the metal, the solid round shape, the worn down imprint of the royal seal cast in its faces. Even the noise it made as it wove through Cash’s phalanges seemed musical and alluring. He wanted to touch it, but his body felt heavy and leaden. He was reluctant to move and break the spell of utter relaxation.

“Getting kinda warm in here, huh?” Cash said, the coin rolling down his knuckles again with a series of staccato clicks.

Stretch blinked, nodding slowly. He hadn’t really noticed it until Cash said anything, but the room was roasting hot. He could feel sweat forming under his clothes, sticky and uncomfortable.

Cash gave a knowing smile. “Maybe take your hoodie off. You’ll feel better.”

He would definitely feel better without the stifling fabric. He should have thought of that sooner. Clumsily, he reached down and started to fumblingly pull the fabric upward, but almost immediately he ran into a problem. Pulling the hoodie over his head would force him to break eye-contact with the coin, and he didn’t want that. He hesitated, swaying uncertainly from side to side.

“Ah, right. Wanna keep watching, yeah? Just cut it off.”

An excellent suggestion. Cash was pretty smart. Stretch formed a small, sharp bone between his fingers and used its keen edge to slash through the hoodie from collar to hem. He gasped with relief as he pulled the suffocating fabric away from his heated bones, immediately feeling cooler, more comfortable. It was his favourite hoodie, a gift from his brother, but he didn’t think twice about casting it aside -- a perfectly acceptable sacrifice so he could keep watching the coin.

Slim made a strange noise, not one Stretch had ever heard from him before, but he couldn’t turn his head to look. It was hard enough trying to keep Cash’s expression in his peripheral vision as his focus narrowed down to the spinning, shimmering disk of gold. 

“Yeah, he’s under,” Cash said lowly, though since it wasn’t an order, Stretch couldn’t fully grasp the words. “Is this what you wanted? Wanna see his pretty bones?”

Slim made another sound, more urgent, a growl that stirred a faint unease in Stretch’s gut. Was Slim okay? Was he having a bad trip? Too much to drink? Stretch really wanted to check on him, but the coin came first. 

“You’re still overheating,” Cash said, his voice louder, more demanding, and Stretch shuddered, almost overcome with the way his bones were burning up. It was almost painful, and he started panting frantically in an effort to ease the discomfort. “You need to get rid of your clothes, but you can’t by yourself.”

His hands had already been half-raised, ready to tear away his top, but his hands could only fist helplessly in the fabric, unable to free himself. He writhed in place, unable to bear the unrelenting heat. He felt dizzy with it, barely able to choke out a desperate, “Please-!”

“Slim’ll help you,” Cash told him soothingly. “All you need is for him to touch you.”

Stretch couldn’t turn to look at his companion, but he could beg with the way his body squirmed, arching in sudden, unforgiving urgency. “Slim, please, you gotta, I need you, please touch me-oh!”

Slim’s hands were suddenly on him, fierce and clawing, his sharp phalanges leaving furrows of dust behind in their hungry grasping, but Stretch didn’t care. He was being touched. That was all he needed. Slim was gonna help him and Cash was there to watch out for them both. He was lucky to have such good friends. 


	2. Keep the tears coming (Fellcest)

**Summary for the Chapter:**

> Papyrus had set the intensity of each device to its maximum, and then locked Sans away for the day, to scream and struggle and cry and know that his only reprieve would come when Papyrus had finished checking all the traps out in the forest. It was in Sans’s best interest to keep them well-maintained instead of slacking off at his guard post, so as far as Papyrus was concerned, he was practically doing a civic duty in keeping his brother motivated.
> 
> \------
> 
> I had a specific idea I wanted to write for a lovely person who donated me some kofis, so this prompt is actually from Day 31 | Crying.

Papyrus was practically humming with anticipation as he returned home from guard duty. His effort to stomp the snow from his boots was more perfunctory than usual, but he was careful to ensure every bolt on the door was properly locked against intruders before making his way up the stairs. For extra security, his bedroom door was locked as well, but the complicated puzzle locks gave way before his experienced phalanges. 

His bedroom was exactly as he left it; immaculately tidy and peaceful except for the muffled sound of whimpers and the frantic rattling of the box at the end of his bed. This, too, was kept locked, though more for securing its inhabitant than against outside interference. Sans had proven that with enough time and determination he could and would slip his brother’s carefully secured bonds and cages. It forced Papyrus to be more stringent with him, an outcome that Sans seemed to encourage despite all his pretence of struggling and swearing.

Papyrus took the special key from his pocket and opened the last lock, prising open the lid and smiling down at Sans. “Hello, brother. Did you enjoy your day off?”

Sans gurgled desperately around the ball-gag Papyrus had lovingly forced between his teeth earlier that morning. His skull was utterly drenched, with saliva, sweat and tears of overstimulation that had completely saturated his blindfold and gone on to drizzle down his face in thick, red-tinted trails. It was already dark inside the box, of course, but Papyrus liked that in this first moment, Sans was still sightless and helpless, unable to know if Papyrus was pleased with what he saw or if he might decide to close up the box and leave Sans waiting for another few, torturous hours before returning. 

He tenderly cupped Sans’s face, and his brother gave a surprised jerk before fervently nuzzling against Papyrus’s palm, likely knowing the gratification of his reactions were the only thing that might save him. His fluids smeared all over his gloves, but Papyrus was used to his Sans’s mess and the effort to clean them later was a worthy sacrifice of his time. He loved the way his brother’s wet magic left vivid, shimmering streaks across the leather, a testament to how devotedly Sans had endured his hours alone waiting for Papyrus to return to him.

“Were you well behaved?” Papyrus asked, as if Sans had any capacity to be otherwise, locked and bound in his tiny prison. Sans nodded fervently, eager to assuage any suspicion, but Papyrus still carefully checked each knot and binding. Everything was just as he left it, tight and secure. One of the benefits of being a skeleton, Papyrus didn’t need to worry about blood-flow or choking hazards. Months of practice had given him plenty of experience in tying knots that not even Sans’s clever manoeuvring could reach. “Hmm, it seems you were. That might be worth a reward.”

From his slick cheekbone, Papyrus let his hand run down the curled shape of Sans’s body, strumming each loop of rope across his brother’s ribs as one might play a finely tuned instrument. Sans’s body thrummed in beautiful resonance, straining towards Papyrus’s touch to little avail. His arms were tied tightly behind him, and the box hindered his efforts to arch upwards. His legs were folded and bound femur to tibia, but Sans parted them as much as he was able, urgently presenting the masterpiece of slick and wires across his pelvis.

Papyrus would have to give Doctor Alphys a special thank you for her creations. The batteries in the bullet vibrators had lasted as long as promised, still excitedly buzzing away against the sensitive planes of Sans’s pubic arch. He had a pair deftly taped to each ischial ring, and a third one strapped right to the back of his sacrum where the vibrations would travel right up his spine with relentless intensity. Papyrus had set the intensity of each device to its maximum, and then locked Sans away for the day, to scream and struggle and cry and know that his only reprieve would come when Papyrus had finished checking all the traps out in the forest. It was in Sans’s best interest to keep them well-maintained instead of slacking off at his guard post, so as far as Papyrus was concerned, he was practically doing a civic duty in keeping his brother motivated.

He didn’t bother to turn the devices off before grabbing Sans’s pubic symphysis hard, letting the tips of his claws dig in to the heated bone. Sans shrieked, jerking with a violent motion that knocked his skull against the cramped wall of the box. All it took was a tight, pinching squeeze and Papyrus could tell by the way Sans’s high-pitched wail turned into a deeper, throatier moan that he was coming. Maybe later, Papyrus would ask how many times the toys had managed to bring him off in the isolation of the box, but exhaustion and numbness would have worn down his sensitivity over the day. Eventually the vibrations alone wouldn’t have been able to satisfy him, leaving him to ride out the unceasing, unchanging stimulation without reprieve.

The way Sans’s body sagged, going utterly limp with relief, was Papyrus’s long-awaited reward.

Still, he left the vibrators running for another long, cruel minute -- watching as Sans slowly came back to himself and realised that his position remained unchanged. Sans whimpered when Papyrus released his pubis, bleating incoherently with soft, pitiful sounds as he tried to beg around the gag. The noises increased in volume and desperation as Papyrus waited, and it wasn’t until Sans’s resolve broke and he descended into wretched, heaving sobs that Papyrus finally gave mercy. 

The remote in his pocket immediately shut the three vibrators down, and without the background hum of their efforts Sans’s cries were even more beautiful. Each uneven breath wracked his small ribcage, and a fresh waterfall of tears cascaded down his cheeks. Papyrus removed the blindfold just to admire the way the tears welled up over the rim of Sans’s sockets, spilling free with each rapid blink as he tried to adjust to the sudden light.

“There, now, brother, you did so well,” Papyrus soothed him, pulling Sans’s small body from the box. He felt so light, so wet and helpless, like a half-drowned kitten pulled from Snowdin river. Papyrus cradled Sans in his lap, pressing fangs to his temple to lick away the salty residue of his tears. “It’s fine, we’re done. You were such a good boy.”

As much as Papyrus enjoyed the build up, the long slow anticipation, the beautiful satisfaction that came with a job well-done, it was possible he enjoyed this part the best; his brother with all his masks, all smirks and sneers and awful, morbid jokes torn down as he cried freely and vehemently in Papyrus’s arms. It would take some time before he calmed down, but until then, Papyrus could hold him without guilt or consequence. It was one of the few reprieves in their dangerous, uncompromising world, and he treasured every moment of it. 


	3. Paid with Interest (Sansby)

**Notes for the Chapter:**

> I ran a poll on my Twitter to ask which skeleton should be the victim for this little ficlet, and Classic Sans was voted for a bad time. 8D So today's poison is non-con Sansby awfulness. You're welcome!
> 
> \-----
> 
> Day 2 Prompt is Drugging | Somnophillia

It’s a slow night at Grillby’s, though nothing out of the ordinary for the small, sleepy town.The dogs were in for their usual post-work poker game, but aside from them only Grillby’s most dedicated customers had dropped by. Still, Grillby waits until precisely his scheduled closing time before flipping the sign on the door and drawing the curtains. He’s already cleaned the slobbery glasses from the dog’s table and swept the floors. The bar is clean and empty except for the one, final customer still slumped over the bar.

Grillby walks up behind Sans, keeping his footsteps light by instinct, but even if he stomped he doubts Sans would so much as stir. Grillby’s had a lot of time to learn the particulars of Sans’s limits. He knows how many glasses of beer will get the small skeleton into a jovial, giddy mood and how many will leave him slurring and maudlin, staring intently into the bottom of his mug like he might find the answers to the universe down there.

Two glasses past the maudlin stage is where Sans begins drooping down on the counter, his skull too heavy to keep upright, and half a glass more will have him entirely insensate and snoring into the smooth mahogany surface. In their unspoken arrangement, Sans won’t question how many times his glass gets topped up so long as Grillby doesn’t bring up his tab. Sometimes he’s curious to know what Sans makes of it; whether he has any unvoiced concerns about the unexpected generosity, or if he really believes Grillby is just a soft touch. Regardless, Grillby’s careful not to leave any cause for suspicion behind, and if Sans has any questions he keeps them to himself. 

For a moment, Grillby leans over Sans and just basks in the simple pleasure of the smaller form beneath him. Sans’s compact, delicate frame is well-disguised beneath his oversized clothes, but Grillby’s seen those bones in all their naked glory and knows exactly how smooth and perfect they are. He breathes against the base of Sans’s neck, his flames swelling excitedly at the familiar mingling of pine and ketchup. The hardest part is keeping the heat of his body in check. Bone isn’t as susceptible as fur or flesh, but he can’t afford to leave marks all the same.

He carefully pulls Sans back against his check, letting the skeleton’s arms fall loose to better ease off his jacket. The shirt beneath is well-worn, with a fresh ketchup stain down the front and a few darker splotches that are probably permanent. It’s the kind of garment Grillby wants to burn to ash, but instead he carefully eases it off, careful not to strain the already threadbare sleeves. Sans is as limp and pliable as a doll, easy to bend and pose as Grillby sees fit. He makes a soft murmur of sound when Grillby takes a moment to indulge himself, running his hands along the graceful sweep of Sans’s ribs. It’s a throaty, agreeable noise, likely appreciative of the warmth of Grillby’s hands in the absence of his clothes. 

The delightful vocalisations are one of the reasons Grillby favours Sans the most. His quiet groans sound wholly like encouragement whenever Grillby strips him down and bends him over the bar. His hips grind readily down into Grillby’s cupped palm, thoughtlessly working himself up with small, uneven motions that are endearing in their desperation. Sans seems like the kind of monster who’d easily have others buying him drinks and taking him home, but his clumsy, ineffective rutting makes it easy to imagine him as shy and inexperienced. Grillby crackles with a churr of encouragement, using his other hand to steady Sans’s spine and help him find a better angle. His own fingers delve into the notch of his pubic symphysis, tweaking the delicate bridge of cartilage there until Sans jerks and his cock coalesces, manifesting eagerly between his legs.

Grillby frowns slightly, though it’s not wholly a setback. Normally, Sans will form a pussy for him, soft, wet and eager, easily plundered with only a little fingering and stretching. His cock will appear more rarely, but Grillby’s learned to accommodate it. His own body is similarly malleable, but though he could form a cunt for himself and ride Sans, it’s not what he’s in the mood for. Instead, he lets his fingers trail back to the still unformed magic swirling beneath Sans’s tailbone. He coaxes it with his fingers until it starts to solidify, swelling outward to fill Sans’s pelvic inlet with a smooth mass centred around a tight, puckered opening. 

They’ll have to go slow if he doesn’t want Sans feeling any peculiar aches in the morning, but Grillby has learned patience in the days weeks and months spent getting Sans to drop his guard. He keeps plenty of oils stocked under the bar -- for a fire elemental, it’s a quick tonic to pep up or to heal the water burns he sometimes gets in the kitchen. He finds one with a light, neutral scent and applies it liberally to his fingers before starting to work Sans open.

Sans’s ass is tight, actively resisting Grillby as he slides his slick fingers gingerly around the fiercely clenched ring of muscle. He’s being careful, but the moment he presses in Sans makes a sharp, uncertain sound. Grillby stares at Sans’s face, trying to gauge if he’s gone too far, but Sans’s expression is still slack with unconsciousness, his sockets closed and jaw hanging loose. There’s a thin trail of saliva seeping through his teeth to pool on the counter, smearing obscenely against his cheekbone which is flushed a lovely bright blue. Grillby tentatively wiggles his finger, and this time Sans just sighs, settled once more into a deeper cycle of sleep. 

_ Gently _ , Grillby wills himself, easing a second finger in. Sans’s inner muscles clench against him, and his cock gives an adorable twinge of interest. By the third finger, Sans’s hole is twitching around him, almost as if it’s trying to suck him in deeper. He pulls them out, ignoring Sans’s displeased grunt, and uses the remaining slickness on his fingers to coat his cock. The oil sizzles delightfully over the surface of his flames, and with agonising restraint he forces his heat back to a mild, barely-simmering warmth. It feels like holding back an orgasm, a titillating discomfort that makes his cock grow harder and his patience grow shorter. He carefully arranges Sans’s body to a more pleasing angle, and presses the head of his cock against that yielding, waiting hole.

He can take his time with Sans, enjoying the exquisite pleasure of a partner who is wholly subject to his every whim and need. Last time Sans didn’t come from Grillby’s slow and tender fucking, and there’s a perverse gratification in knowing that he doesn’t need to be considerate of Sans’s pleasure. Sans won’t know either way; his body is a willing, pliable receptacle for Grillby’s personal enjoyment. Beyond the pains he takes to ensure he doesn’t damage Sans in any way, Grillby can do as he likes so long as he carries Sans home afterwards to his long-suffering brother. 

And it might take him a day or two to recover from the hangover, but Sans always comes back, walking through Grillby’s door with a smile and a joke, never questioning the fresh glass Grillby will have waiting for him on the counter. 


	4. Sleep with the Fishes (PuppyMustard)

**Notes for the Chapter:**

> I love a good Merskeleton AU. :9 Vore is one of those interesting kinks I enjoy dabbling in, because it's so challenging and varied. 
> 
> Warning: This can definitely be interpreted as fatal vore, but if you want to envision a happier end where Slim changes his mind or just swallowed his little catch as part of a greater plan to give him a safe place to rest and heal, go right ahead. 
> 
> Day 3 Prompt is Vore.

If he’d been given any other choice, Red would never have gone down into the Blackwater crevice. Everyone knew it was a deathtrap, full of violent currents and crushing pressures, but it was those precise deterrents that Red was hoping would protect him. The surface-dweller’s net that had tangled around his tail had left a deep lattice of oozing wounds that would have attracted every predator in his home-waters. He’d torn off one of his own fins just to get free, crippling his ability to swim with any meaningful speed. All he could do was wait and hide and hope desperately that his wounds would close before he starved to death.

It had been two days already since he’d eaten. With momentous effort, he uncurled from his tight ball of agonised misery and peered out of the tiny cave he’d found in the craggy wall of the crevice. Outside, the waters were dark and ominously still, but hunger was starting to win against his paranoia. If he didn’t keep up his strength, he might die of his wounds regardless, and despite all the horror stories he’d heard he had yet to see anything alive in the trench besides himself and some strange looking algae that had glowed in the dark. 

He would prefer a fat, fresh fish, but the algae might be edible and would be an easier meal to catch in his current state. He eased himself from his hiding place, hissing at each small movement of his tail. The colder water of the crevice was helping suppress the blood flow, but his upper torso didn’t have the protective covering of his ecto-flesh tail, and he felt the chill keenly as it passed through the slats of his ribs.

He couldn’t keep himself properly afloat without his tail. Instead he had to crawl and climb across the shelf-like ledges of the crevice, working back to where he remembered finding the slimy garden of algae. It was a slow, exhausting journey, and more than once he nearly slipped to fall down into the seemingly endless pit of darkness beneath him. At this depth, his gills were already straining to filter the dense water. He couldn’t afford to go any deeper without risking suffocation. 

Finally, he caught sight of the soft, pale glow coming from a ledge above. Desperation made him clumsy, and he let out an obscene shriek and a curse as he accidentally knocked his tail against an outcrop in his climb, but at last he pulled himself over the slippery edge and found himself face-first in the thick blanket of algae.

The glow was a little off-putting, but its color was a rich green and he was too hungry to deliberate over its edibility. He yanked free a spindly tendril of vegetation and scarfed it down, wincing at the slimy texture. It was a little bitter, but otherwise tasteless, and he could feel his magic gratefully absorbing that first mouthful so he kept going, clawing eagerly at the mossy tangle and shoving the shoots into his mouth. There was little finesse as fumbled through the tangled bed of greenery, blindly hunting for the longest, thickest stem to quell his appetite.

When his hand closed around a particularly large, firm tendril, he was only thinking of what a satisfying mouthful it would make, and it wasn’t until he’d brought it all the way to his mouth that he realised the texture was wrong. He paused in his ravenous feasting to stare at it. At first glance, it looked like an ordinary vine, albeit a plump one, but the texture under his fingers was rubbery and firm. He prodded at it curiously, and its’ green luminescent coloring rippled and shifted to a color that was closer to orange. A booming chuckle sounded from above him, far too loud and too close for comfort.

“Heh. That tickles.”

Red jerked towards the voice. For a moment, his wild gaze couldn’t find the source. It was only when the creature shifted that he realised its dull, bony face wasn’t part of the crevice wall, and most of the plush mass he’d mistaken for algae was actually a bed of seething tentacles, one of which he was holding. 

“You’re down deep, little one,” the creature -- another mer, Red realised belatedly -- told him. Its tentacle squirmed in his grip to wind around his wrist, taking a firm hold. “Didn’t they warn you it’s dangerous down here?”

“F-fuck,” Red stuttered, scrambling backwards, not caring it it meant plunging over the edge and into the abyss. “Oh shit, get off, get off-!”

The tentacle on his arm put a stop to that, winding tighter to draw him back in. He clawed at it madly, but couldn’t seem to penetrate its thick, rubbery skin. The mer watched his efforts with amusement, chin resting lazily on its arms. “Did you lose your pod, little one, or did they abandon you when you became a liability?”

“Neither!” Red snapped, almost as irate as he was terrified. “Not that its any of your fucking business, but I don’t have a pod. Don’t fucking need one either.”

The giant mer made a sympathetic sound even as another tentacle rose from the camouflaging mass of algae to capture Red’s other arm, holding him with ease as if he were a child in the arms of an adult. “So there’s no one to miss you or mourn you. How sad.”

“Wait!” Red yelped, the word practically squeezed out of him as a thicker, more powerful limb circled around his ribs. The suckers on the underside of the tentacle nipped at his bones like tiny mouths suckling against him. He jerked violently, his injured tail thrashing weakly in the water. He could smell the rising tide of his own blood, feeding into his panic. “D-don’t, please, I’m sorry, I’ll just leave, you’ll never see me again!”

“That would also be sad,” the mer told him, its tentacles lifting Red closer to its face. Up close, he could see a long crack running through their mandible. A shattered tooth had been replaced with a rough equivalent of gold, like the surface-dwellers sometimes did. It only made the mer’s face even more fearsome, the crooked fang distorting its every expression into a hungry leer. “We don’t see many pretty fish like you down here. Such a lovely color.”

Red had been so distracted by all the tentacles he hadn’t realised that, like him, the mer also possessed a fully skeletal upper-half with arms and hands just like his own. It reached out a long, spindly hand to run a surprisingly graceful phalange down the length of his crimson tail, stopping just short of where the net had gouged through his flesh. With a thoughtful hum, it plucked one of the torn, ragged scales from the edge of the wound, making Red yelp at the sharp sting. The flaking fragment was brought to its mouth, and a long, sinuous tonge bearing the same suckers as its tentacles flicked out to capture the scale, bringing it into its mouth. It considered the taste, and smiled with an expression of blissful contentment. 

“My usual catch is much smaller than you,” the mer said, turning its satisfied gaze on Red. The colors on its body were shifting and rippling, more orange appearing amongst the green in hypnotising swirls of color and light. “It’s been so long since I’ve had such a feast, and look at you. Freshly bleed, like you were a gift just for me.”

“I…” Red wants to struggle, to fight and scream and beg for mercy, but the mer’s voice is low and calm and the ripple of its colors are soothing. He’s so tired, exhausted and hurting, but the pain seems to recede wherever the mer is touching him. Looking down, he can see a darker, inky color seeping from where its suckers are wrapped around his body. Some kind of poison, his thoughts offer dully as his head lulls forwards, going limp. “Don’t…”

“Shhh,” the mer hushes him. “It’ll be fast. Peaceful. Painless. Just relax.”

Red can’t do anything else. He feels numb, his skull floating like he’s too close to the surface, breathing the thin, oxygenated water. He doesn’t even feel the scrape of the mer’s sharp, needle-like teeth as it distends its enormous maw to accommodate the breadth of his skull and shoulders. He thinks he hears its jawbone dislocating, popping free to increase the stretch, and some distant part of him is giddily grateful it didn’t choose to bite him into more manageable chunks. It swallows him whole in one long, gulping motion, drawing him into the tight passage of its throat. Pressure squeezes all around him, but instead of claustrophobia or terror it feels nostalgically comforting, like a long-forgotten embrace. He doesn’t remember the parents or pod he must have had to raise him to a survivable age, but he thinks their care might have felt something like this.

He falls, descents, floats gently through the clenching tube until it releases him into a new, wider space. He still can’t stretch out, forced to coil around his mangled tail, but it feels natural to curl up like he would for resting. He feels protected and safe, no longer scared or desperate or full of dread and apprehension for how he’ll survive the next few hours. It’s peaceful and quiet. Letting go and falling into sleep feels like the most natural thing to do.


	5. Tender Mercy (Swapfell Papriel)

**Notes for the Chapter:**

> I'm running polls on my Twitter to choose the focus character for some of these fics, so come join me at [@Askellie_ut](https://twitter.com/Askellie_ut) if you want to nominate some upcoming victims. For this prompt, Swapfell Papyrus was the chosen character, so have some Swapfell Papriel. :9
> 
> Day 4 Prompt is Fucking Machines.

Two hours seems a suitable span for the first leg of the punishment. Toriel descends into the dungeons with stately grace, in no particular hurry. The basement lights are kept dim and static on purpose, leaving the cells in perpetual, unchanging gloom, but the floors and walls are absolutely spotless. She’s no heathen; her dungeons are clean and well-cared for, though they rarely see use. Any crime worthy of her attention has only one viable punishment. It would be unseemly for a Queen to descent among her people and murder indiscriminately, farming her subjects for the XP needed to remain in power, but righteous execution needs no justification. Only her Judge’s guilty verdict.

Her lovely Judge is currently the only occupant of the dungeon, and even from the far end of the corridor she can hear the sweet sounds of his cries. She takes care not to quicken her step, knowing if he has any wits left he’ll be able to hear the echo of her approaching footsteps. He must still retain some small measure of sanity, because his wails go softer, restrained to short whimpers and pained grunts. By the time she arrives at the door to his cell, he’s practically choking on his efforts to bite back the filthy sounds that spill from his throat, though whether it’s in respect to her presence or some paltry effort to retain dignity, she can’t be sure.

“Hello, my Judge,” she greets, warm and gentle as she is with all her subjects, even the ones who are destined to meet their end on the spikes of her trident. “How are you faring?”

Papyrus blearily opens his sockets, twisting his neck at a painful angle to look up at her looming visage. His jaw moves wordlessly, issuing nothing but sharp, hitching breaths with each forceful jolt of his body, but he manages to whisper with surprising clarity, “Poorly, my Queen.”

She laughs, delighted by his courtesy. “Then have you perhaps changed your mind about your Judgement?”

He closes his eyes, his body shaking with a violent tremble that seemed like it might break his fragile bones apart. With intense concentration, he slowly shakes his head, refusing her demand despite how much the effort clearly costs him.

Her expression melts from kindly patience to hard displeasure. “Are you sure? I am quite convinced that Chancellor Madjick must be guilty. If I can see it, surely you can also.”

He shakes his head again, straining hard against the restraints that hold him to the floor, forced in a painful bow of supplication. His head rests at her feet, and only his pelvis is forced aloft at a cruel angle that leaves him immobile and defenceless against the machine behind him whose piston moves with simple-minded rhythm. In and out, forcing its way deep into the manifestation of pseudo-flesh that fills the space inside his pelvic cavity. The end of the pison is blunt and thick, and for his defiance she had denied him any lubrication or preparation before it had speared him the first time. There’s plenty of fluid now, though whether it’s only his arousal or some equivalent for blood she isn’t sure. 

The manifested magic between his legs was as bright as a bonfire, flaring with light and heat, but so long as she doesn’t touch him with an intention of release there was no chance of him reaching his climax. The machine had been built to precise specifications, each component crafted to arouse, to plunder, to punish, but not to permit satisfaction. She’d had it made solely for him - a special device for her beloved Judge, whose HP was too low for him to be punished in the traditional sense.

She gives a deep sigh, letting her disappointment be known. “That is truly a pity. I was sure that a little time to think would allow you to discern the error of your ways, but it appears you need to contemplate the matter further.”

“My Queen, please,” he says, his voice strained and soft, phalanges scrabbling mindlessly at the floor. “He’s not guilty, I’ve seen his soul. P-please have mercy-”

“The throne requires his death, my Judge,” she tells him harshly. “His LoVe makes him a risk to my position, and his XP will be enough for me to achieve my next Level. If not him, I’ll require several lesser sacrifices to ensure my safety. Is not one death for the good of the Underground better than several when our population already struggles to maintain itself.”

Papyrus whines at her, or perhaps from the particularly brutal way the machine thrusts into him. Tears have welled up over his sockets in fresh splatters to match the pool that’s formed beneath his knees. Her pristine floors are dirty now. Perhaps as a final punishment she’ll have her Judge clean the mess himself once he comes to his senses. In many ways, Papyrus is still very much an innocent, unaware of the heavy choices a ruler must make for the good of their people. For that reason, she chooses to go easy on him. His punishment is hardly a brutal one, though it might feel that way to him now. 

“He’s not...guilty,” Papyrus gasps, no longer able to maintain the composure to speak to her clearly. She watches with interest as his body writhes and jerks, fighting the cruel compulsion of the machine as it pushes him to the edge of a climax he’s unable to reach. “You can’t ask for guilt when there is none-”

“I can,” Toriel says simply, kneeling down beside him. “I can because you are a judge, but before that you are  _ mine _ .”

She touches his skull with the full, unassailable knowledge of her ownership and possession of his precious, unique soul. She thinks of how, when he realises the error of his ways and gives himself to her in sweet surrender, of how she will take his ravaged body and clean it with her own benevolent hands. She will teach him how much more rewarding it is to please her when she takes hold of his brutalised flesh and brings him pleasure to match and exceed all that he has been denied so far.

He screams as her intention finally brings him to long-denied climax, his body convulsing with a rictus that looks like agony. The piston never stops, continuing its relentless rhythm, and even before his climax ends Papyrus is howling and babbling incoherently, forced right back to the edge he’s been riding for hours. He kindness isn’t a reprieve so much as a torturous reminder of what he’ll continue to be denied until he meets her demands.

“Think some more,” she tells him, though it’s hard to know if he can hear her over the sounds of his own suffering. “I’ll return in a little while and we can discuss the matter further.”

Another two hours, she thinks as she departs. By then, she’s sure he’ll have come around to her way of thinking, and she can ease him through the aftermath with the care and affection his obedience will deserve.


	6. Sowing seeds (FloweySansPapyrus)

**Notes for the Chapter:**

> Today's skeleton victim was lovingly chosen by my Twitter audience. :D Come join us if you want to vote for who'll be the focus of upcoming chapters. For this prompt we have a delightful non-con mix of Punflower/Boneblossom/Fontcest. 
> 
> Day 6 Prompt is Oviposition | Force Feeding.

Sans knows he should look away, shut his eyes, turn his head, _ANYTHING_ but stare with horror and awful, wretched curiosity at the vines wrapped around his brother’s cock. There’s a bizarrely beautiful contrast of the lively green of the plant and the sultry orange of Papyrus' ecto-flesh against the crisp white snow of the forest floor, but he shouldn’t be staring at it. He shouldn’t watch as the vines twist and tighten, stroking with a sinuous unnatural grace. He shouldn’t be fascinated by the way the wriggling bloom at the end of a vine has closed over the weeping head of Papyrus’s shaft, milking his essence. He can see the trail of glowing come trickling down the inside of the vine as if it’s a tube to be collected in the bloated body of what seems to be the flower’s main stem.

Sans is no biologist, but he’s pretty sure no flower in existence looks like this: with a thick, rubbery bulb growing from the base of its roots, translucent leaves coquettishly shielding a bounty of large, round seedpods that are being liberally watered by Papyrus’s collected come. Then again, no flower should leer like that, its face distorted with curiosity and wicked intent as it looks at Sans as if it’s found its next meal.

Staring at the weird, bulging seed sack is marginally better than watching his brother be violated. Sans manages to redirect his gaze with difficulty, struggling to speak around the restraining vines strangling his cervicals. “So, uh. Don’t know how to tell you this, but if you’re looking to be a daddy I don’t think that’s how you’re supposed to germinate.”

A thousand puns about using the wrong kind of seed run through Sans’s mind and he hates himself for every single one.

“Oh, I know,” the Flower says, its surprisingly toothy smile widening. “But you know how magic is. Sometimes it just works. Besides, if anyone could do it, surely it would be the Great Papyrus!”

Sans risks another glance at his brother and fights a wince. There’s tears in his brother’s sockets, but also a kind of dazed exhaustion. His brother has magic reserves to spare, but having his essence forcibly materialised and sucked out of him is swiftly draining them. The smell of his strenuous arousal, a musky spicy, permeates the clearing. There’s barely any fight left in him, only the weakest twitches and the occasional muffled whimper that manages to escape from the knot of vegetation wrapped around his jaw. His reluctance to truly harm the Flower, no matter how much the despicable weed deserves it, had ended the fight before it had truly begun.

Sans has no such compunctions, but between the Flower using Papyrus as a shield and his own weak stamina, he’d barely managed one attack before tripping over its hidden net of tendrils lying in wait beneath the snow. The vines have torn through his clothing, burying themselves in the spaces between his ribs and spine. He’s one careless twist away from turning to dust himself, barely able to move anything besides his mouth which is a poor weapon against the Flower’s gleeful determination.   


“Okay, that should be enough,” the Flower declares. With an obscene, wet sound it pulls its sucking vine off Papyrus’s abused cock. Even despite the number of times it’s made him cum, Sans can’t help but notice his brother is still half-hard, but he tries not to think about it. He’s torn between relief that the Flower is finally finished with its perverse embezzlement, and dread at what it might want to do next.

“Cool,” Sans says, trying to sound nonchalant. “Now you let us go and we all go home, yeah?”

The Flower chuckles at him. “No, silly. Now we test a new theory! It’s like science. You like science, don’t you, Sans?”

“Nope,” Sans replies quickly. “Pretty sure I don’t.”

“Aww, that’s a shame,” the Flower coos, mocking. “See, I’m a big fan of experiments. Like, remember that time I gave you one of those human drinks I found in the dump?”

Sans gives the Flower a hard stare. “I’ve never met you before in my like.”

“Oh yeah. Oops.” The Flower doesn’t sound especially sorry. It waves a vine as if dismissing that small discrepancy. “Well, when you drank it, your body did something really cool I’d never seen before.”

Yeah, Sans knows that trick. Sometimes it’s useful for keeping hold of things he doesn’t want to put in his pockets, and Papyrus always looks so hilariously outraged when he does it. He’s watching the Flower’s face carefully, looking for weakness, but that doesn’t mean he’s unaware that the tentacle that had been previously molesting his brother is slithering its way over to him, the petals at its opening still dripping with orange-tinted come.   


Sans looks at the vine, its tube-like stem, and the fat body of the plant filled to bursting with seeds in an embryotic bath of come, and comes to an awful, unwanted conclusion. “So you think I’m a good place to sow your seeds, huh?”

The Flower makes disgusted face. “I really hate your puns.”

“I kind of hate that one too,” Sans admits. “So how about you, uh, go find a greener pasture. Go fertilize a nicer garden. Maybe plant your-grk!”

The sneaking vine unceremoniously shoves its way into his mouth, making Sans immediately regret not keeping his teeth clenched. He tries to force it out with his tongue only to be immediately overwhelmed by the confrontingly salty-sweet taste of come. His brother’s come. His sockets go wide, his body locking up in sheer denial, giving the vine plenty of opportunity to worm its way deeper into his skull. Petals brush against the back of his throat, making him choke, and reflexively he can feel his body building a path for the inorganic matter to go. The tendrils looped around his body shift and make way for the manifesting organs filling out his empty pelvic cavity. They cradle around his new belly with ticklish interest as Sans grunts and swallows around the vine, trying to evict it from its uncomfortable, invasive depth.

“Are you ready?” the Flower asks brightly, and Sans cringes in horror. He sure as hell isn’t in any way ready for the sight of the first seed making its way cheerfully down the vine’s stem. Up close, it’s much bigger than he’d thought. It’s shaped like a walnut and about the size of an orange. He tries to shake his head, as much to dislodge the vine as to broadcast his explicit refusal of what’s about to happen. He bites down, but the stem doesn’t even bend beneath his teeth, leaving the tube clear and unobstructed as the seed passes through and is forcefully objected in the back of his throat.   


It’s stuck there for a moment, fighting against the constriction of Sans’s pseudo-muscles, which have never attempted swallowing something so large and ridgid, but the judicious lubrication of Papyrus’s magic is an unwanted facilitator. It takes several agonising seconds of choking before his throat finally yields, his body accepting the intrusion. The seed is a hard knot of painful distension sliding its way down his throat. It’s almost a relief when it finally reaches his stomach. It settles into his gut with tangible, uncomfortable weight.

“That’s one,” the Flower says, dragging Sans’s attention back from the horrified discomfort of his own body. “I think I have...oh, maybe three dozen more. I wonder if you can fit them all?”

Dusting first might very well be preferable, but no matter how Sans struggles, snarling and cursing around the thick stem, the vines adjust their hold to keep him gently, carefully restrained as the tube starts to fill with a mainline of unstoppable seeds headed straight for his stomach. 


	7. Sharing is Caring (Red/All Papyuses)

**Notes for the Chapter:**

> I'm running a little behind in these ficlets, but I should be able to catch up in a day or two. ^_^ 
> 
> Day 7 Prompt is Face Fucking.

“Are you ready, Runt?”

Red flexes his wrists, testing the bonds. The ropes Boss has used are new ones, scratchy and stiff with no wear or washing to soften and loosen them. He’ll be wearing fresh scour marks and bright hot abrasions by the time they’re finished. It’s a sign that although Boss might be willing to share him, he wants his marks branded all over Red’s body as a bold, undeniable claim.

Red nods, for once keeping his comments to himself. There’s no talking when Boss is using that tone. All he wants from Red is his complete silence and submission. Nerves have made his mouth go try, and he swallows rapidly to coax the saliva back to his tongue. He’ll need as much of it as his body can spare.

“Very well.” Red can’t see through the blindfold, but he hears Boss moving, the heavy tread of his leather boots on the carpet. The door opens, and the background murmur of laughing, teasing voices from beyond goes immediately silent. Red holds back a grin. Boss sure knows how to shut up the rabble when he chooses to make an entrance.

“I’m treating you filthy cretins to a gift,” Boss announces with grandeur. “Treat it with respect...though no need to be gentle.”

There’s a bubble of amusement among their audience, and the room fills with the sound of eagerly whispered arguments over who gets to go first. Red struggles to sit placidly, trying to keep his bones from rattling. It’s not that he doesn’t trust Boss to keep him safe; rather, he’s worried of disappointing his brother, of not being of adequate use. He digs his phalanges into the knots Boss has tied for reassurance, so distracted that he doesn’t realise the argument around him as been resolved until a nudge beneath his chin tilts his face up towards his first customer.

“Hey Sweetheart,” Stretch says, playfully throwing Red’s favourite endearment back at him. Red bares his fangs to show what he thinks of that, but when Stretch’s thumb hooks in the corner of his mouth he yields instantly. His teeth part, tongue extending like a red carpet invitation, soft and plush.

“Damn,” Stretch breathes, sounding a little in awe. His clothing rustles, hastily pushed aside, and the muted smells of sweet honey and cigarette ash are suddenly amplified, hitting Red’s nasal cavity in a rush that almost makes him dizzy. Beneath Stretch’s natural scent, there’s a familiar musky undertone that makes Red’s mouth water. Suddenly his saliva isn’t having any trouble welling up, leaving him almost drooling in eagerness. A warm, firm shape presses against his cheek, the texture of ecto-flesh more forgiving than bone, and tingling slightly with the magic used to conjure it. “You really want this, huh?”

In answer, Red angles his head and swallows Stretch’s cock in one long, hungry gulp. Stretch makes a startled noise, reflexively catching the sides of Red’s skull, though Red’s already taken him as much as possible, his nose almost brushing Stretch’s pubic symphysis. 

Behind him, Boss lets out an amused chuckle. “Is he too much for you, Ashtray? And here I thought you knew what you were doing.”

“Shut up,” Stretch hisses, his grip tightening delightfully on Red’s skull. Boss knows what he’s doing, and that simple, cutting remark is all it takes to strip the lazy patience away from Stretch. He yanks Red back with unexpected strength, and when he starts to thrust, each motion is a jolt of aggravated frustration that slams into the back of Red’s throat. He lets himself go limp, trusting himself to the fury of Stretch’s pace and Boss’s watchful eye. 

When Stretch comes, he pulls out just enough to release his load right on Red’s tongue, and it’s a desperate race to swallow it all before it starts to overflow. Red groans gratefully, dutifully licking the shaft and head clean of release. It must be too much stimulation, because Stretch releases him, stumbling back with a curse, leaving Red feeling bereft.

Though not for long. New hands take hold of his face, turning him to a new angle. The ghosts of dust and maple tickle his nose with the fur of the coat in front of him. He’s surprised; Slim is usually the quietest and meekest among the Papyruses. Red had expected him to go last, the fervent brush of a hard cock against his face demonstrates that he’s no less eager than Stretch had been. 

Red’s mouth is open, waiting, but Slim chooses to tease him first, rubbing pre-come against his cheek and tracing the outline of his sockets beneath the blindfold. Red huffs at him, playfully chomping his teeth in aggravation, but when Slim finally gives him what he wants Red’s mouth is forgiving and careful. His tongue lies flat, and he gives a delighted shudder when he realises Slim’s shaft is pierced. There’s a ladder of hard, metal bolts along the underside that promise to brutalise Red’s throat. He can almost feel Slim’s crooked smirk as he takes hold of Red’s skull and starts to test the pliability of Red’s throat with a few warm-up thrusts. 

Slim’s taste is more bitter than Stretch’s, quickly drowning him out. His cock is longer too, reaching a new depth in Red’s throat that wakes some vestigial, unnecessary instinct that tries to panic at the possibility of choking. Red bears through it, focusing on how the ropes are sawing at his bones with each rocking motion, giving him a stronger, more demanding discomfort. Between his legs, his own pubis symphysis is hot and aching, magic roiling around the bone unformed. If it were Boss in front of him, the hard, steel-toed point of his boot would settle there, applying cruel pressure, but Slim’s hold doesn’t stray past his collarbones. Boss’s rules, probably. They can fuck his face, but no more than that. The rest of his body is off-limits. 

It takes Slim a minute to find his momentum, but when he does, he too forgets gentleness in favour of burying his cock as far down Red’s throat as he can. Red groans encouragingly around him, his muffled sounds turning ragged each time Slim’s piercings gouge into him. His skull is ringing sweetly, and he drunkenly thinks he’ll have to talk to Boss about getting something similar.

To his disappointment, Slim doesn’t come down his throat, instead pulling out just a moment before his release so he can spill over Red’s face. He gasps at the unexpected heat of it, mouth open to catch any stray droplets that might fall into his mouth, but there’s not nearly enough for his satisfaction. 

“Oh Cherry.” Strong, bony arms pivot him in a new direction, and the movement makes the ropes bite into him sweetly. Careful hands smear the cum on his face, spreading it with fascinated curiosity rather than cleaning it. “He made such a mess.”

“Heh. Sorry,” Slim says, sounding anything but.

“Well don’t worry,” Papyrus promises him grandly. “I won’t be nearly so inconsiderate.”

Red mewls approvingly of this decision, opening his mouth once again. Papyrus’s shaft is thicker than Slim’s, the taste both creamy and salty, and there’s a familiar, demanding aggression to his hold as he starts to thrust with an enthusiasm that promises greater stamina than his companions. He hopes by the time Papyrus finishes, Stretch’ll be ready for another round. Boss promised him a relentless pounding of cocks to suck until he’s satiated, his body swollen and tingling with cum. His body aches with how badly he wants it, and he imagines he can feel Boss’s gaze on his back, searingly intense and heavy with his hard-won approval.


	8. Dirty Dollars (MoneyMustard)

**Notes for the Chapter:**

> This isn't quite in the spirit of Kinktober since I didn't write this fic recently, but it's an old commission I haven't had the chance to post before and it's a perfect fit for the prompt which gives me a good excuse to finally release it from my fic-vault. Warnings for extreme dub-con and dirty, gross assholes having dirty gross sex.
> 
> Day 7 Prompt is Photography | Video Taping.

Red’s hands are trembling as he pulls the stocking up over the thick ecto-flesh wrapped around his thigh. It’s not nerves, he tells himself with furious insistence. It sure as fuck isn’t fear, even though Cash’s hungry leer looks almost demonic in the dim lighting of the sleazy motel room. The fact that he’s been stripped bare, naked except for the delicate nylons (with lace trimmings on the garters, fucking ridiculous) might have been terrifying for a lesser monster, but that’s definitely not Red.

The burning behind his eye-sockets is fury, he’s sure. Anger is a totally justified and reasonable response to this situation.

“Fucking disgusting pervert,” he snarls, the consonants wavering unevenly. He can’t quite bring himself to look at Cash. His gaze slides all over the dirty floor, taking in the holes left by cigarette burns and the plethora of unidentifiable stains. “Bastard. Filthy sicko.”

“Yeah, go ahead and call me pet-names if it gets you hot, babe,” Cash croons gleefully. His tongue has slithered out over his teeth, glistening unwholesomely with slobbering interest. With a smooth motion he lifts the video camera up to cover his good eye. Its’ cold mechanical lens is somehow worse than Cash’s drug-hazed eyelight. His yellowed fingers tap nimbly over the controls, and a green light starts blinking cheerfully in Red’s direction. “But I’m done with foreplay. Bend over, bitch, and show us what you’ve got.”

Red’s face is already burning with embarrassment, but the heat feels worse than staring into one of Hotland’s lava pits. It’s hard to draw in air, which is surely why his voice sounds far too high and thin when he asks, “W-what?”

The blow comes from nowhere, cracking him across the jaw with a brutal snap of impact. Red wheezes, wildly checking his stats, but despite the force of the hit, his pitiful HP only dropped a single decimal point. All the Papyruses have that control, although it’s a lot more terrifying in Boss and Cash than it is in Honey and the CreamPuff. Cash hasn’t moved at all, but the bone he’s summoned glows menacingly over Red’s shoulder, not yet disappearing.

“That’s just a warning,” Cash says, his voice dropping into a menacing octave, reminding Red of why he’s paying the bastard for protection. “Time is money, babe, and tonight you’re mine, so bend over like a good little whore and don’t make me ask again.”

Red doesn’t think twice. He bend with clumsy haste, his body shaking with adrenaline. There’s nothing seductive or measured in the movement, but Cash makes a small noise of approval which allows Red to release the painful breath he’s been holding. With Cash’s gaze fixated on his ass, Red reaches up to touch his aching face. His fingers come away wet. There’s a thin trickle of blood leaking from his nasal aperture, and he thinks one of his teeth has come loose because there’s more trickling down his chin. His mouth feels too dry to summon his tongue to lick away the sticky mess, so he moves to wipe it with his knuckles.

“Leave it,” Cash orders. “You look better like that anyway. Spread your asscheeks for me. I want everyone to get a nice look at this fat ass of yours.”

A pitiful sound slips out from between Red’s teeth -- part whimper, part bitten-off protest. The dull glow of Cash’s bone attack casts a sickly halo over his bones, urging him to reach back with shaking hands to cup the generous curves of his ass. He’s never summoned this much of his ecto-body before, and already he hates it. There’s so  _ much _ ; thick, flabby folds weighing him down, making him feel bulky and helpless instead of insulated and protected like he might have hoped. Almost viciously, he digs his fingers into the squishy curves and resentfully spreads himself wide.

“See, was that so hard?” Cash asks. Red wisely chooses not to answer, struggling to hold himself in such a humiliatingly exposed position without trembling too violently. “Now how about you finger yourself for me.”

Liquid trickles from the underside of Red’s chin to splatter on the floor beneath him, joining the already innumerable stains. He can’t tell if it’s blood or just anxious sweat condensing off his overheated bones. He should be telling Cash to go jump off a waterfall, but instead all that he dares to voice is a meek and perilous, “L-lube?”

“Nah.” Red doesn’t need to turn to picture how Cash must be smirking. “I bet that slutty hole of yours doesn’t need it. You’re so loose you could probably take my whole fist dry, right?”

The speculative way Cash airs the suggestion makes Red think he might damn well attempt it if Red doesn’t hurry up and comply. With that unpleasant motivation in mind, he forces his fingers to creep forward, seeking blindly down the cleft of his asscheeks until his phalanges find the upraised pucker of his entrance. He nudges it tentatively, trying to find the courage to stick a finger in. Despite Cash’s crass claims, Red’s ass is unplumbed territory. In his cutthroat universe, he’s never had the gall to fuck around, especially not with so much of his magic tied up in his stupid, useless ecto-body instead of free to form attacks or teleport him the fuck out. 

What little he knows tells him to expect pain, and it doesn’t help that his body is tense as a strung wire as he tries to delicately tease himself open, flinching at the unfamiliar pressure. 

Cash gives him a long, merciless minute of graceless fumbling before finally losing his patience. “Jeeze, you’re really fucking useless, aren’t you? Can’t even fuck yourself properly.”

“S-shut up!” Red hisses, his fingers groping faster but no more effectively at the taunt. He’s barely managed to wedge the tip of a finger in, and already his eyes are wet from the effort. A lifetime of low HP has taught him to shy away from the slightest hint of pain. The slim finger wedged into his asshole doesn’t even qualify as that yet -- only a tingling stretch -- but he just can’t bring himself to push further. His breath hitches in an uneven, ugly sob. 

“If this is too hard for you, I know another way you can work off your debt,” Cash offers, the sweetness of his tone at odds with the smoke-roughened hoarseness of his voice. 

Something like hope wells up in Red’s soul, and he almost slips on the greasy carpet in his rush to turn around. “What can I-?”

He stops, the words sticking in his mouth, because Cash already has his cock out, stroking it lazily, without shame. The camera is propped up on the table, still blinking amiably in his direction even if Cash is no longer interested in wielding it. His gaze is only for Red, his single eye locked hungrily on the smaller skeleton’s plump frame, fangs pulled back in an eager smirk. 

Red’s wordless stare only makes Cash grin wider, smug. His fingers glide slickly over the head of his cock, spreading the oozing drops of pre-come. “Impressive, isn’t it? So how about you let me fuck you with it.”

The bright sheen of his magic is the color of amethysts, a hue that might have been beautiful if it weren’t taking the shape of a thick, ribbed shaft that looked almost disproportionately huge compared to Cash’s lanky frame. Red belatedly thinks to close his gaping jaw, unwilling to concede he’s a little bit in awe of Cash’s generously sculpted magic. It certainly puts his soft, dumpy figure to shame.

“Are you kidding?” he squeaks. “You’d fucking kill me with that thing.”

Instead of looking insulted, Cash looks even more pleased. "C’mon, you know I’ll be careful with you. Can’t have my favourite little cash cow dusting, can I? All you gotta do is lie back and take it, and we’ll call your debt squared. How’s that sound?”

Red knows better than to look in Cash’s eye and be ensnared by the hypnotic swirls lurking in his sockets, but that leaves him staring at his cock instead. Trying to imagine that monstrous thing fitting inside him makes his knees feel weak even as his gut does a curious backflip that isn’t entirely uninterested. Cash is disgusting, but not wholly unattractive despite how much he resembles the Boss. He’s a filthy slob, but even if he rarely shows it he’s got the same ruthless precision and excruciating control, and it’s not the first time Red’s wondered how else those skills might be applied.

Before he has much opportunity to contemplate it further, Cash pipes up again. “Cuz, doll, I’ve gotta be honest with you...your cam skills leave a lot to be desired. You ain’t gonna be paying off anything if I can’t find a buyer for your sweet little sex-tape here, and frankly you haven’t given me anything to work with.”

Cash pats the camera fondly, arching a brow at Red. “Of course, if you’ve changed your mind, I can always go talk to your brother about a payment plan-”

“Fine!” Red snaps, gesturing frantically as if to physically draw Cash’s attention back from that awful possibility. The last thing he wants is for Boss to know about his debts. He’ll fuck his way through Cash’s entire universe to keep that from happening. “Fucking fine! You can...do whatever you want...”

The last words trail off in an uncertain mumble, and he hadn’t thought his face could burn more furiously than it had when Cash had ordered him to bend over. Cash rises from the bed, all long-limbed, predatory grace, like a spider. In two strides, he’s confrontingly inside Red’s personal space. With the difference in their heights, the head of his cock is level with Red’s nasal aperture, and he can smell it; the oily, salty tang of Cash’s sex overpowering the less appealing smells of unwashed bones and cigarette smoke steeped in his clothes. 

“Just one more thing,” Cash says, reaching into his pocket. Red’s sullen glare blanches into shock as Cash loops a thick belt of leather around his throat. It’s not  _ his  _ collar, the one Boss gave him. That one is lying coiled up beneath his scattered clothing like an angry snake in hiding, out of sight and mind as much as Red can make it. Cash’s collar is brand new, stiff enough that the leather’s already cracked to fit around his thin neck, but from the feel of it, it’s similar. There’s small, studded spikes along its length, and a loop at the front, already attached to the leash in Cash’s hand. 

“...wow,” Red manages after a moment, trying to sound derisive. “I didn’t realise that was your kink, pal.”

It’s the wrong thing to say, he realises too late. Cash’s face clouds over, all pretences of pleasant cajoling and patience evaporating faster than an ice floe in Hotland. He yanks hard on the leash and Red chokes as he’s lifted from the floor, dangling painfully by his cervicals as Cash sneers into his face.

“Listen, bitch, I’m the one doing you a favor here.” Angry spittle and foul breath assault Red’s face as he scrabbles madly at the collar. Skeletons don’t need to breathe, but the extra weight he’s carrying from his ecto-flesh makes him feel like his cervicals are splitting apart. His feet kick blindly, unable to touch the floor, but after one furious shake like he’s a naughty puppy in need of discipline, Cash throws him back against the bed. Red collapses back onto the mattress, curling pitifully in on himself with a snivel of fear.

“M’ sorry!” he whimpers, hands coming up to protect his face from any incoming blows. Cash growls, climbing on top of him, and as pissed as he looks, Cash is still brutally hard. The terrifying length of his cock grinds meaningfully against Red’s stomach, leaving a slick trail of fluids. The small jagged spines on his length scour painfully against Red’s ecto-flesh, like a dozen tiny claws.

“Not yet you’re not,” Cash growls, shoving Red’s thighs, easily contorting the smaller body beneath him. He pauses for a moment, breathing heavily and looking down at where Red’s much smaller cock is also standing to attention, completely in defiance of the horror and dread coursing through his marrow. He’s more panicked than aroused, but the smell of pre-come and naked manhandling are apparently enough to fool his libido. Cash’s hips roll in a slow, sinuous motion that grinds their lengths together, and the raw scrape of the spines is both awful and exquisite. Red’s eyelights roll, and he lets out a guttural moan.

“But you will be,” Cash promises, folding Red’s knees back up to nearly his ribcage, angling his cock to slide along the exposed groove between Red’s legs. The broad head of his shaft catches on the lip of Red’s entrance, much more fearsome and demanding than his fingers had been, and Red doesn’t even have the breath to voice his objection before Cash changes his angle and starts pushing in with aggressive efficiency. 

“FUCK-!” Red screeches, clawing blindly at Cash’s clothing, his body seizing like he’s grabbed a live wire. It hurts almost that much, pain burning through his marrow with the same blinding spark that leaves him trembling and jerking, unable to stay still. “FUCK! FUCKING FUCK! STOP! CASH-!”

A large hand smelling of semen and cigarettes slaps over Red’s jaw, forcing it shut. “Quit screaming, you pussy, you’re fine.”

His HP isn’t shifting, that’s true, but Red still feels like he’s dying. Even though his ecto-flesh feels like it’s going to tear, Red knows logically that it’s far more elastic and resilient than real flesh. That knowledge is no comfort at all when the spines on Cash’s dick are scraping his insides raw, and the broad head of his cock feels like it’s distending his non-existent organs. Glancing down, he can see the muddled hue of it moving inside him beneath the surface of his ecto-flesh. Each inward thrust brings Cash impossibly deep inside him, the dark shadow of his cock nearly breaching the bottom of his rib cage. 

“Nhu-uuuuu...” Red whimpers from behind Cash’s hand -- a mistake, because in the next moment Cash’s fingers are in his mouth, pressing down hard on his tongue. Red chokes around them, tasting their bitter salt and the overwhelming, musky flavor that must be Cash himself. Just as he’s wondering if he dares to bite down, Cash’s phalanges find the cap of the bar pierced through Red’s tongue and give a vicious yank. Red is wholly unprepared for the rush of almost violent pleasure that stems from where his tongue is rooted to the back of his jaw, all the way down his spine to his overstuffed pelvis.

“Oh! You like that!” Cash crows, sounding delighted. He pulls again, this time adding a cruel twist that forces Red’s tongue into a painful spiral. He should hate it, but he almost can’t think through the flush of searing arousal, giving an utterly whorish moan as his cock twitches excitedly against his belly. 

Whatever Cash says next -- something disgusting or degrading, no doubt -- is lost to Red. All he can think of is how his body feels, mouth and asshole stretched, the aching strain of holding Cash’s pulsing shaft and the way his tongue piercing is being toyed with, Cash’s filthy fingers squeezing and wrenching at the bar in a way that feels careless but somehow makes Red’s skull reel with bliss. 

Dazed, it takes him a moment to react when those clever fingers are suddenly withdrawn from his mouth. He makes a wet, unhappy sound, blinking furiously up at Cash who’s wrapping the leash back around his fingers.

“Spoiled little shit, aren’t you? Making me do all the work,” Cash complains, giving the leash a sharp yank. “You’ve had enough fun. Now it’s my turn.”

Cash pulls out only enough to have better leverage for turning Red’s limp body over, and the sensation of swivelling around on his cock makes Red wheeze out a strangled, incoherent sound. His face is pressed down hard into the musty mattress even as Cash pulls back on the leash, the collar pinching tight around his cervicals until it feels like his skull is about to pop off the end of his spine. His instincts are screaming at him to fight it -- all it would take is once careless tug and Cash’ll be fucking nothing but a pile of dust -- but his body feels like a stringless marrionette. He can’t remember how to move or how to shape a bullet even to save his life, because at this new angle Cash’s cock feels somehow impossibly bigger. His lower half is still trembling from the agonising stretch, another part of him is still riding the unfortunate high Cash’s demanding fingers wrenched out of him. He’s unable to do anything but sob and drool into the sheets as Cash angles his hips at a punishing angle and proceeds to plough into him at a relentless pace.

Despite the pain and his low HP, his body has somehow decided to embrace brutal handling. Not even the vicious scrapes of the spines on Cash’s cock rubbing him raw are doing much to quell the rising tide of pressure and need in Red’s gut. His own cock is throbbing, begging to be touched, but Cash has lost all interest in Red’s reactions. His only focus is his own pleasure, his grunts ragged and animalistic as he grips Red’s hips hard enough to leave bruises, fucking him with a ruthless urgency that slowly obliterates all sense and reason from Red’s mind, leaving him bonelessly pliant.

With a bit more time, he might have been able to get off even without a hand on his dick, but the timeless ordeal seems compressed into an instant, and suddenly it’s over with a hot flood of Cash’s magic spurting into him. There’s so much, he can feel it overflowing before Cash even pulls out, his belly bloating and the excess oozing down his thighs. More drips out as Cash slowly withdraws his cock, giving a pleased sigh and rudely wiping his wet shaft off on Red’s ass before dismissing his magic entirely. 

“Not bad,” he says, giving Red’s hip a dismissive shove, sending him sprawling onto his side in a limp, flushed tangle of bones. “That fat ass of yours isn’t totally useless after all. I’d even say it’s worth a little something extra.”

Red’s cock is hard enough to hurt, rivalling the throbbing ache of his stretched asshole. Cash’s words make him whine hopefully, but instead of reaching between his legs, Cash delves into the pocket of his hoodie and withdraws a handful of coins. He carefully counts out three of them, dropping each onto Red’s panting, exhausted body.

“That should do it,” Cash says cheerfully. “Maybe next time, work on that attitude of yours a little. No one likes an uppity little fucktoy.”

There’s a smear of jizz on Cash’s shorts that he attempts to wipe away, only managing to leave a more diffuse stain that doesn’t seem to bother him much as he turns to leave. “I’ll leave you to take care of cleaning up the room, honey. Make sure you get all the stains out. If I don’t get my deposit back, I’m adding it to your bill.”

Too choked up with arousal and disappointment, Red doesn’t manage to find his words until the door is shut and Cash is well and truly gone, leaving him lying in a filthy puddle of sweat, saliva and semen that’s swiftly growing cold and disgusting over his bones. 


	9. Slither (Underswap Papyrus/Tentacles)

**Notes for the Chapter:**

> Inspired by the absolutely amazing artwork of @hj_skb, which you can find [here](https://twitter.com/hj_skb/status/1182428548126171136). Once I saw this gorgeous piece, I couldn't stop thinking about it, and felt compelled to write a matching fic to go with such a deliciously drawn idea.
> 
> Day 8 Prompt is Tentacles | All the way through.

After more than thirty minutes of fumbling around in the gutted undersides of the machine, Papyrus finally finds what he’s looking for. It’s a single, frayed wire, slightly scorched where the rubber coating has melted back to bare its copper innards. He quickly grasps it between his phalanges as if it might try to escape now that he’s finally cornered it.

“Gotcha, you little bastard,” he gloats, deftly splicing in bypass for the worn connection. It’s these tiny victories that keep him coming back to the machine even though he’s still not entirely certain what he’s expecting it to do. It’s like solving a puzzle, one cracked circuit board and severed wire at a time, and some day he’ll finally get to see the completed picture.

He gleefully wriggles his way out from the lower access panel, holding his hands out placatingly towards the unresponsive monitor. “So, how about it? You gonna finally talk to me, babe?”

The machine ignores him, like it usually does, but Papyrus has learned not to be offended. He likes to think that one day, it’ll come around to his playful sweet-talking and persistent care. He flicks the main switch, hoping for that quiet background hum that means the machine is channeling power once again. What he gets instead is a loud, electrical pop followed by every light in the basement simultaneously going dark.

“Damnit,” he mutters, deflating in disappointment. Thankfully Sans is out at Alphys’ and won’t be back until tomorrow. Papyrus doesn’t know how he’d explain blowing out the power in their house and half of Snowdin  _ again _ .

Except that he can still hear power humming somehow, a background murmur in the dark. He flinches as sudden lights blind his sockets, and as he blinks to clear them he can see the monitor flickering with unexpected life. With a reluctant hiss of static it finally settles on a dark screen with a single line of stark white text.

** _Synchrony Established. Connection opening. Gateway resonance at 11%._ **

“Oh shit,” he breathes, leaning closer. “You’re actually talking.”

The number at the end of the text is swiftly climbing, as is the plaintive whine of the machine. It reaches 18%, then 26% before rapidly jumping all the way up to 44%. For a moment, Papyrus just marvels at the confronting proof that all his efforts have actually achieved something. It’s gratifying, but the longer he stares at the screen, the more the racing number unnerves him. The thrum of the machine begins to sound less like mechanical effort and more like a rising scream of warning.

“Okay, cool, that’s great and all, but y’know, this relationship is progressing a bit faster than I’m used to,” he babbles, reaching out to tap frantically at the buttons around the screen, hoping to interrupt its progress. None of them seem to have any impact. “How about we slow things down a little? I kinda want to get to know things better before I make a commitment, so how about you-”

He freezes. The number on the screen has already reached 100%, and a second line of text has appeared.

** _Connection open. Anomalous entry detected._ **

The frantic wail of the machine cuts out suddenly. The silence is somehow more unnerving. There’s no other sign of change, no lights or sounds other than Papyrus’s own heavy breathing. The rest of the basement is still dark, but suddenly it doesn’t feel empty.

“Yeah, I’m out,” Papyrus says, retreating hastily from the machine, telling himself there’s no shame fleeing when he has no idea what he’s dealing with. This is definitely the time to go and get Undyne, and maybe his brother in case this is the sort of situation that needs someone who can actually take a hit to their HP. 

He’s barely taken a step when his ankle catches on something in the dark, sending him tumbling backwards. He lands on his tailbone with a curse, kicking wildly to free himself from the obstruction. It feels like a cable, a long, coiling weight tangled around his foot, stubbornly refusing to dislodge itself. It’s not until he reaches down to yank at it that he registers the cold, slick texture of it that absolutely has no place in the basement workshop.

“What the…?” He gives it a bewildered squeeze, and horrifyingly, it squeezes back, undulating in his hands in a slippery wave. He drops it with a startled yelp, frantically wiping its slime off on the front of his hoodie.

The monitor casts just enough light that he can see the silhouette of it coiling up around his leg -- a fat, wet tendril reaching out from behind the machine. If it’s attached to a body, he can’t see it, but as it tightens its hold on him he can see more wriggling appendages making their way towards him, slithering across the floor like a pack of shelless Thundersnails in a disgusting, terrifying race. 

“Whoa, hey, no, get off-STOP!” His rising volume and panic only seems to attract the tendrils to him. They lithely dodge his flailing limbs, latching onto his free leg and winding around it until the sheer weight of them has him pinned. For all their size and liveliness, their slippery skin is shockingly cold. It’s like being dunked up to the waist in Snowdin river, his bones tingling with a chill that’s starting to escalate from mild discomfort to dangerous numbness. 

The reason it’s spreading so quickly, he realises with belated alarm, is that its thick mucus is eating through his clothing, dissolving the fibres like spun sugar evaporating on the tongue. For a moment, his body seizes in mindless dread, expecting his bones to melt just as easily, but even though there’s long rents in his hoodie where he wiped his hands clean, his fingers seem intact. Maybe it doesn’t work on bone, or maybe it just takes longer. Either way, he doesn’t want to be around to find out.

“Let go!” he snarls, summoning a sharpened bone to impale the thick tendril now wrapping itself around his bare femur. The attack simply bounces off its tough hide, the magic splintering apart. The beast remains unharmed, but not unaffected, and there’s a violent surge of new movement as it reacts to the threat. Before Papyrus can even think to try again, he’s yanked across the floor, deeper into its grasp so more of its questing appendages can crawl up his body. His clothing is shredded to pieces as they forcefully delve into the spaces between his bones. 

“Euuugh-AHH!” His grunt of revulsion rises into a cry of shock as a particularly rude tentacle slobbers its way over his hip, curling around the base of his illium to take a firm hold of his spine. Its hold keeps him from bucking away as his cargo pants begin to decay under the insistent groping of its brethren. It takes them only seconds to eat away at the thin barrier of fabric, and suddenly there’s nothing protecting his pelvis from their aggressive exploration. The first cold lick of an appendage on the underside of his sacrum makes him gasp, his protests turning into a garble of incoherent sound as more and more begin to thread their way through his pelvic cavity, filling its narrow circumference to bursting fullness. 

He can’t think straight enough to form another attack. In hysteric denial, he claws madly at the appendages, trying to get them off, get them out of him, but their slippery, writhing forms simply catch hold of his wrists, tangling around the radii and ulnae and pinning him to the floor with their inescapable weight. He can feel squirming feelers climbing up through his ribs, taking ownership of the empty cavity of his thorax like unwanted organs. The way the cold moves up his body makes him feel like he’s sinking, his body leaden with the chill and the creature’s suffocating hold.

It’s like a nightmare -- surreal and terrifying -- and in a desperate, child-like impulse he cranes his head towards the stairs to shriek for his brother, “SANS!”

But Sans is with Alphys, and opening his mouth is a mistake that only invites one of the tendrils to force its way up through the bottom of his skull and out through his teeth. He gags, unwillingly tasting the salty-sweet tang of its mucus as it brutally slithers its way out of his mouth, curling around his skull like a gruesome crown. He chokes, gagging on its thick, rubbery body, barely able to breathe. Its intrusion through his skull makes his head feel light and fragile, the painful cold stabbing up behind his temples. He can’t move. His vision is wavering as consciousness loses its hold. 

_ Help _ , he thinks weakly, unable to voice it, or do anything to fight the swallowing tide of slimy limbs moving on him, around him and through him, claiming every inch of his body in its hungry clutches. 


	10. Imperserverence (Underfell Papster)

**Notes for the Chapter:**

> This is one of my favourite, but more obscure kinks. :9 Primarily this ficlet is Underfell Papster, but there's implications of Sanster and Fellcest here too. 
> 
> Day 9 Prompt is Cum Milking.

Papyrus’s expression is a mask of concentration. If not for the furrow between his brows and the beads of sweat trickling down his skull, he might almost seem unaffected. Gaster watches unabashedly, his smile curling in delight at his subject’s admirable but futile resistance.

“Not ready to give me what I want?” he asks, enjoying the jolt of tension that runs through Papyrus’s posture. “Your brother gave in so much more easily.”

It’s a calculated remark to garner a reaction, and as predicted Papyrus opens his eyes to glare with furious ire. The sound he makes might have been a savage growl if not for how thin it is, ragged and strained with the effort of holding back a litany of much more shameful noises. 

“Do you want me to tell you about it?” Gaster questions pleasantly, patiently. He hardly minds the delay. It’s much more interesting, watching Papyrus be worn down by excruciating increments. 

Strategic placement of the electrical stimulators ensure that no part of Papyrus can completely escape the current. At first, he could manage to hold himself still with a disciplined rigidity that was almost impressive, but now sheer exhaustion has wrought fine tremors in his limbs. Every joint is glowing brightly, his bones rubbed raw by each of their neighbours, serving only to heighten his sensitivity. He’s lasted longer than expected, but Gaster doubts he can endure much more. 

“He began his session very much as you did,” Gaster reminisces fondly. “Cursing. Shouting. Threatening my life. He was quite creative. Eventually I had to gag him.”

“Stop,” Papyrus says, his voice soft and dangerous, but wholly ineffective. Thick manacles keep his wrists and ankles pinned taut at each corner of the table. His most furious struggling has already failed to release him from their bondage. He’s no threat, and they both know it. 

“That made him much easier to deal with. I imagine he would have tried to bite me as I removed his clothing,” Gaster continues, his fingers tingling with the memory of smooth, warm bone bucking against him. “Have you seen his naked body? It’s flawless. No scars...but then, he never could take a hit. If not for that broken tooth, his body would be perfect. It’s beautiful, really, don’t you think so?”

“Stop,” Papyrus repeats, this time with less strength and more desperation. How many times has Papyrus looked at his brother and thought the same thing? It’s an interesting question worth revisiting later, when his subject is more compliant.

Papyrus’s bones are beautiful in their own way, despite the nicks and gouges that mar their surface. They’re a tapestry of violence across the thick, strong bones, proof of Sans’s love for favouring his brother with better nutrition in their formative years. When his current experiment is over, Gaster will indulge himself and touch them more to see how Papyrus will squirm. He’s looking forward to it. 

“Of course, that means he has no fortitude when it comes to pain. When I turned on the stimulators,  _ oh _ , how he writhed, how he  _ cried _ . Tears pouring from his sockets. He tried to beg, I think, but ah. The gag made that quite impossible.”

He leans over Papyrus, careful not to touch. The heat of his nearness and the faint pressure of his magical aura are enough. “He came for the first time in under a minute. It was quite a spectacular sight. His soul is just as unblemished as his bones, and so very, very bright.”

Papyrus’s tremors have become more violent, his bones audibly rattling. His jaw is clenched fiercely shut, but not even that is enough to silence the faint, high-pitched whines clawing their way free of his throat. 

Carefully, so very carefully, Gaster guides his hand into Papyrus’s ribcage to hover over his trapped soul. The clear plastic case is fitted tightly to its surface, keeping it fully enclosed in a suffocating sheath. Its’ only allowance is a clear plastic tube that runs from the crux between the two round lobes of the soul’s shape, applying faint suction to collect each drop of essence as it condenses on Papyrus’s core. So far, he’s only collected a few stray drops as Papyrus fights against his climax with every ounce of willpower he possesses, but inside its tight enclosure his soul is throbbing and pulsing, straining against the plastic. It’s glutted with pent up magic, almost at its limit. It’s tempting to touch, to caress the trapped organ to see how readily its first release might spill, but ah...that would ruin the experiment. Regretfully, he withdraws his hand. 

There’s few ways to truly milk pure essence from a monster, but forcing extrusion through the soul is one of the most efficient and least harmful. Sans and Papyrus should be grateful for his mercy.

“Would you like to see what he gave me?” Gaster asks, not bothering to wait for Papyrus’s answer, assuming he’s still coherent enough to give one. He’s quite proud of the outcome of his first experiment. He retrieves the sealed capsule from the table and brings it close. The liquid inside sloshes carelessly, noisily, with a sound that’s viscerally obscene. “Look at it.”

Unwillingly, Papyrus does, his sockets drawn almost helplessly to the container filled with his brother’s essence. The liquid is a bright silver-white, the color of monster souls and their raw magic, but there’s traces of Sans’s own red-tinted residue swirling throughout. With a deft twist of the lid, Gaster opens it up to release the pungent smell into the air. It’s rich and musky, Sans’s own personal scent magnified to an almost overwhelming degree. Gaster breathes it in, savouring the wet desperation and shame of it, the animal urgency as each successive climax had driven Sans into mindless ecstasy and agonised exhaustion. 

The smell seems to hit Papyrus like a physical blow, his whole body jerking with what looks very much like pain. A choked cry escapes him, and just with that, his soul swells and explodes with a flash of light, a miniature solar flare. The plastic case distends with the sudden flood of liquid, some of it flushing through the collection tube, but there’s too much for it all to be drained at once. Papyrus’s contorted expression twists further, his fresh release compounding the pressure on his soul, basting it in its own frantic, aroused essence. It keeps him suspended on the threshold of that climax, drawing it out to an agonising length as the tube unhurriedly draws it away.

It’s a minute that probably feels like years before the intensity finally subsides, leaving Papyrus panting and shuddering on the table, his brave composure evaporating entirely. Gaster smiles down at him, admiring the healthy measure of magic now resting in the collection beaker. It’s only a fraction of what he collected from Sans, but one release isn’t enough to complete the process. The process will continue, each successive climax amplified and extended by the one before, until Papyrus’s soul has nothing left to give. 

“It took more than an hour for me to finish with your brother,” Gaster tells Papyrus, settling in to watch the proceedings. “I wonder how long you’ll last?”


	11. Friends with Benefits Pt.2 (HoneyPuppyMoney)

**Notes for the Chapter:**

> A continuation of Chapter 1 of this Kinktober series. 
> 
> Prompt is Spit-roasting | Gangbang.

Physically, Stretch and Slim were very similar, more so than their other cross-universal alternates. The only traits that set them apart were Slim’s cracked mandible and false tooth, and the fact that like most of their Fell-verse counterparts, his phalanges ended in sharp points instead of soft, rounded tips. 

Those claws made swift work of Stretch’s clothes, shredding the seams and tearing them off rather than trying to coordinate them over clumsy limbs and the sticky sweat of Stretch’s body. Stretch didn’t care about their destruction, only for the absolute relief brought by virtue of having so much more bare bone on display. Each of Slim’s careless touches was like being gifted with a cool breeze or a bite of nice-cream in the middle of Hotland. It was the only reprieve from the smothering heat of the room that only he seemed to feel.

“You love this,” Cash told him, and though it wasn’t something Stretch had ever thought about wanting, it must be true. His body was wracked with an ecstasy that made thinking nearly impossible. “You need to be touched. Your body wants to be filled up and used.”

It was such an obscene observation that Stretch couldn’t help flushing even as his magic coiled in his pelvis. He didn’t want Cast to be right, but even though he struggled to keep his magic contained, he was too overwhelmed for control. His pussy manifested in spite of his best efforts to prevent it, already aching with the need to be stretched and stimulated.

“Hands on the floor,” Cash directed when Stretch tried to reach back to give any sort of relief to this throbbing clit. “You can’t touch. Slim’s the only one who can help you.”

Stretch sobbed helplessly at the unfairness of it, hating his body, his own ineptitude, but of course Cash was right. Nothing Stretch could do would be of any help. He leaned forward, burning face resting on the carpet, pelvis raised up and on display in a silent plea for assistance.

But he should never have doubted that Slim would understand, because almost immediately the other was there, pressing up against his tailbone. The tent in his pants was a wordless affirmation and promise that he knew exactly what Stretch needed and would willingly provide. It was enough to make Stretch whimper in relief, head crooked at a painful angle to make sure he didn’t lose sight of the coin. That would be the only thing worse than Slim not helping him when he needed it the most.

He leaned back, grinding into the covered bulge he could feel at the front of Slim’s jeans, broadcasting his willingness without the mortification of needing to say anything, but to his dismay Slim’s grip on his hips forced him still. He couldn’t understand the hesitation until he heard Slim asking, “You?”

Cash made a dismissive sound. “This is your night, sweetheart. He’s all yours.”

Stretch tried to buck backwards, but Slim’s hold was stronger than expected, keeping him close but immobile. His voice was sly, coaxing, “We could share?”

Cash’s normally unassailable composure wavered, showing a fraction of hesitation, and Slim assertively offered, “His mouth is just as pretty as his cunt. Don’t you want to try it out?”

Even while he was thinking, Cash kept his coin moving through his fingers in elegant leaps and gravity-defying spins. For a moment, Stretch forgot his desperation, fully enamoured with the way the bright speck of gold glittered, filling his vision until he couldn’t see anything else, couldn’t move, couldn’t think-

“Are you listening?”

Cash’s words sounded like they came from miles away, but each syllable cut through the haze like a deliberate caress across the surface of Stretch’s soul.

“Yes,” he answered dazedly, his body tight and tense, primed for any demand or order.

“Everything that’s about to happen is something you want. It’s something you asked us for. You don’t need to think about it, you just need to know that you need it and you love it,” Cash said him, his voice oddly deep and resounding, ringing in Stretch’s skull until he couldn’t hear anything else. “You’re so turned on, you can’t stand not to be touched. You want us to have you. You want us to use you. You’re gonna stay like this until we’re ready to send you home, and when we’re done, all you’re gonna think about is how grateful you are and how much you enjoyed it.”

“F-fuck,” Stretch whimpered, his vision basked in beautiful, glorious gold. The only things anchoring him to reality were Cash’s orders and the exquisitely agonising arousal burning through his marrow. He’d never been so aroused, so mindlessly desperate for it, but even though his body is wracked with painful need, he kew he was in good hands. Saliva welled up in his mouth, thick and wet with greed. “Please, please, PLEASE, Cash, I need-!”

“What do you need, honey?” Cash asked, and the blinding gold in Stretch’s vision disappeared. Cash’s empty hands were under his jaw, guiding his face up, scrutinising Stretch’s expression carefully. For a moment, Stretch forgot himself, blinking in befuddled confusion, wondering when smoking and drinking had suddenly landed him on his hands and knees, but then Slim ground against him from behind and the tidal wave of his arousal crashed into him once again, 

“You!” Stretch breathed, fumbling blindly for Cash’s hips, tugging at his clothes. His body shook with how much he burned for it, like a junkie in need of a fix. “I need you in me, right now, fuck-!”

Cash laughed, and Stretch distantly thought he could hear a tinge of relief in it. That didn’t matter nearly as much as getting Cash’s shorts off to unveil the tantalising purple glow he could see gleaming through the fabric. He freed Cash’s cock with reverent care, mindful that as much as he needed it, Cash was doing him a favour. He stroked the shaft generously, delighting in the way it grew harder under his touch and Cash groaned, taking a firmer hold on Stretch’s skull. 

“That’s right, honey, I’m all ready for you. Show me what your mouth can do.”

There was a distant, almost irrelevant flash of something like alarm reminding Stretch that he’d never done this before. A time or two, monsters had propositioned him at Muffet’s and tried to coax him into the alleyway behind her bakery, but even though the idea had excited him, he’d always liked to think that his first time would be special in some way. It would be someone who loved him and cherished him, who wanted to treat him right…

He wasn’t sure if he could really say that Cash or Slim loved him, but they were going to give him everything he needed, and surely that was enough. He opened his mouth, letting Cash guide his skull to accept the thick breadth of his cock onto Stretch’s waiting tongue.

The taste was a long stronger and more confronting than he expected, and he almost embarrassed himself by reeling back in surprise. Then the bitter, salty flavor hit his senses like a jolt of caffeine and he groaned hungrily, gulping Cash down in wet, clumsy swallows, trying to remember what he’d learned from illicit Undernet porn vids about how to pleasure a partner’s dick. 

Gentle with the teeth. Make it as wet as possible. Try to take it in deep. The last was the most challenging since it required manifesting a throat and learning to apply suction on the fly, but Stretch thought he was doing good job from the Cash cash groaned, his fingers scrabbling enthusiastically over Stretch’s skull. Stretch’s sockets were half-mast in pleasure, feeling strangely satisfied just by having Cash’s cock in him, like his body was made just for this purpose. 

It would be even better, he thought, if his pussy was just as full. Slim seemed to have forgotten that he was in the middle of something, poised against Stretch’s tailbone in frustrating stillness. Cash noticed as well, letting out an uneven chuckle. “Y-you just gonna watch there, sweetheart?”

Encouragingly, Stretch flexed his hips backwards, the lips of his pussy catching on Slim’s covered erection, making them both hiss at the frisson of contact. Mortifyingly, Stretch could feel his own wetness soaking into the cloth, his magic already embarrassingly slick. Thankfully, Slim was jolted into action, hastily shoving his jeans down to free his cock which he thrust readily along the sensitive planes of Stretch’s slit. 

“Oh, he likes that,” Cash observed, grinning salaciously. Eyelights blown and jaw slack, Stretch could feel tears welling up in his sockets because it was so incredibly good but also utter cruelty that Slim was so close but not in him. He gurgled a complaint, but with Cash’s cock so far down his throat the sounds he made were wet, obscene and senseless. “I bet he’ll cum just from taking you.”

Stretch’s phalanges fisted against the floor -- he couldn’t touch himself no matter how painfully his clit was throbbing for attention, for reasons he couldn’t quite remember. He felt like he was going mad with the need to climax, his bones rattling in a frenzy of urgency, saliva dripping heedlessly down his chin and throat. When Slim finally angled against him just right and started pushing in, Cash’s prediction proved itself true, and Stretch let out a muffled cry as his cunt spasmed and pulsed through the most intense orgasm he’d ever experienced. 

His vision seared white, a color almost as mesmerising as the gold that glittered in his memory. His soul felt full to bursting, paradoxically heavy and weightless in his chest as he shuddered through the relentless surge of pleasure. The brutal feeling of Slim’s cock fighting against the clenching of his passage to bury itself in him kept him riding the high until it was almost unbearable, squirming and sobbing between the other two skeletons as he was achingly breeched at both ends, his body the tool of their pleasure. 

“Damn,” Cash breathed, sounding awed. 

“Fuck,” Slim agreed. His cock was fully buried in Stretch’s pussy, a deep and aching invasion that barely registered in the delirious aftermath of that first orgasm. “He’s so tight.”

“Yeah,” Cash replied, holding Stretch’s skull steady on his limp and strengthless spine to give a shallow thrust. His cock was twitching in Stretch’s throat, little ticks of anticipation. “We’re gonna ruin him.”

Stretch’s body was lax between them, warm and pliant. He had exactly what he needed, Slim and Cash both inside him, both making use of him, and not even the faint twinges of discomfort and filthy, sticky aftermath of fluids between his femurs could detract from his sheer relief. He was floating dreamily, satiated and content even as his body still tingled with the promise of more.

Almost seamlessly, Cash and Slim found a gratifying rhythm, their strong hands guiding his unresisting body back and forth, taking turns to plunder his pussy and his throat. He could hear Cash grunting above him, filthy sounds of satisfaction as he pushed further down Stretch’s throat with each thrust until Stretch’s nasal ridge was practically bumping against his pubis. The difficulty he’d had earlier trying to convince his throat to open up seemed to have vanished. His body yielded easily, barely hitching even as the flared head of his cock scraped rawly at the back of his mouth.

Slim had a firm hold of his spine, using it as a handle to roughly pull Stretch back onto his cock with punctuating jolts that all three of them could feel. Every movement was a slippery glide accompanied by equally vulgar sounds. Stretch couldn’t keep quiet, purring with guttural, pleading sounds around Cash’s shaft with each deep, demanding thrust. He didn’t think it could get any better when, abruptly, Slim let out a ragged grunt and came, burning hot seed spilling deeply in Stretch’s body. His eye-lights blew out in ecstasy, and his expression must have been to Cash’s liking because the other skeleton pulled out of his throat with a curse only to aim his cock and cum all over Stretch’s face, bathing him in glistening purple magic.

“Yeah,” Cash said, his voice soft and rough, looking down at Stretch with an expression of possessive delight before turning his grin towards Slim. “You have the best ideas, sweetheart. Wanna swap holes?”

“Fuck yes,” Slim agreed, and Stretch gave an eager moan of appreciation as his body was unceremoniously flipped over and positioned for another round. 


	12. Lock and Key (Kustard)

**Notes for the Chapter:**

> Prompt is Forced Chastity!

“Hey there, buddy.”

Red leaned against Sans’s back, too hot, too chose and too abrupt for any defence. He was radiating smugness like he was his own miniature sun of depraved glee, leering right in Sans’s face. It took every ounce of resolve for Sans to keep up his own bored, unaffected expression, though the way he was sitting upright and stiff in the chair of his guard station probably didn’t fool Red for a minute.

“Hey,” he replied, his voice pitched almost half an octave lower than usual, raspy like he’d spent the night smoking and drinking in New Home. “I’m on shift, which means you’re supposed to be in shift, right?”

“I’m on break,” Red said with intractable confidence. “So I thought I’d mosey on over and see how my favourite bed-buddy was doing. You okay there? Comfortable?”

His hands circle around Sans’s waist, settling companionably on the crests of Sans’s illium before steadily creeping lower. Sans tried to keep it together, but as Red knowingly traced the lip of his pubic bone he couldn’t help giving a little shudder. By the time they were slinking along his pubic arch, it was less of a polite tremble and more of a wracking jolt.

“Fuck,” he breathed as every nerve in his body sounded off like a series of firecrackers, over-excitable and way too optimistic. The cock cage Red fastened on him that morning was ingenious, a marvel of engineering, with more puzzle locks on it than Papyrus’s private magazine collection. It had so far resisted Sans’s best (albeit half-hearted) efforts at removal, and he doubted Red was here to let him off easy.

“You’d like that, wouldn’t you?” Red rumbled, leaning harder against Sans’s spine, pressing him with inexorable gravity towards the counter of the guard station. “I mean, I’m all for it. I could fuck you right now, leave you full and dripping with my cum to go along with your new accessory. Maybe in a couple of hours I’ll even let you loose.”

The idea of Red railing him right out in the open, blowing his load and then leaving Sans high and dry, painfully aroused and utterly unable to touch himself, sounded nearly unbearable. They had a safeword for exactly this reason, but Sans chose not to use it as he let Red bend him over and start tugging down his shorts. 


	13. Made to fit (Swapverse Papyrus/Muffet)

**Notes for the Chapter:**

> Prompt is Fisting!

“Um, Muffet,” Papyrus begins, trying to sound calm and rational and absolutely not like he’s freaking the fuck out. “Can’t we talk about this? Maybe come up with a payment plan? I swear, I can come up with the money in a couple of days-”

“That’s what you said last month, dearie,” she trills sweetly. “And the month before. If you like, you can consider  _ this _ a kind of payment plan. After all, with the size of your tab, you’re definitely not going to work it all off in one session.”

“Yeah, uh. About that.” His horrified sockets are stretched as wide as dinner plates, but the entirety of his vision is narrowed to the dance of Muffet’s nimble fingers as she slicks her delicate hands in a thick, shimmering oil. “What, uh...what’s that for?”

“Preparation,” Muffet tells him primly. “I’ll be renting your body out to my customers, and some of them might be a little bit much for a beginner like you. It won’t take you long to learn the ropes...oh! Was that a pun? Surely you liked it.”

“Yeah, aha, v-very funny.” It’s decidedly NOT humorous when it’s his body dangling from her ceiling, trussed up in spider webs. A small army of spiders are doing the work of unravelling his clothes for her, one loose thread at a time, slowing leaving him exposed. His femurs have been pulled apart at angles that are a strain even for someone without ligaments, leaving his pelvic cavity bare and unprotected. “But seriously, I didn’t mean to forget, I promise I can-_AUGH your hands are cold!_”

“Sorry, dearie,” she coos, sounding anything but. Her slippery hands skim the underside of his pubic arch and tailbone. “Now, are you going to be a good boy for me and show me your magic?”

He whines, feeling the demanding tug of her intent, impossible to fight because on some level he knows he banked too much on her generosity to ignore the debt he’d hoped would somehow resolve itself before he had to pay it back. His pussy manifests itself, unfamiliar and heavy in his pelvis.

“Well done! Now, there’s a technique to this. We start small-” She gestures to the hands down her right side. The topmost arm is slightly thinner and more delicate, with each set of limbs becoming thicker and stronger as they descend. Her lowest fist is almost the size of his own. “-and by the last set, you’ll good to go. Are you ready?”

“No!” he squeaks, but the protest goes unheeded. He yelps in pain and dismay as she presses her clenched hand to his entrance, slowly but unrelentingly forcing it into his cunt. 


	14. Show Off (Black+Edge/Slim)

**Notes for the Chapter:**

> Prompt is Cuckolding!

Slim sat on all fours, struggling not to fidget or squirm. The vibrator in his pussy was making that a difficult task, but Black had been firm. Slim’s pussy would be twitching and well-lubricated, the sexual equivalent of putting out the welcome mat, when Edge chose to make use of him. His body had been made ready, and Slim was desperately eager to be a gift worthy of the praise his brother laved upon him.

“No need to hold back,” Black said, standing at a close but comfortable distance. He would be merely an observer, present to keep Slim safe and enjoy the mess Edge would make of him. “I promise you, he’s well trained.”

“I’ll be the judge of that,” Edge said, and though he sounded gruff, Slim could pick up the same strain that hinted his composure wasn’t as effortless as he was trying to make it seem. He looked down at Slim, his already imposing height made more so by the intimidating heels on his boots. The hands he used to take hold of Slim’s skull were so much larger than Blacks, engulfing and powerful. The tantalising strength in them had saliva welling up greedily in Slim’s mouth as he parted his teeth, offering his tongue and throat for Edge’s service.

Edge’s cock was just as magnificent as his filthy imagination had promised, and there was gratifyingly little kindness in the way he hilted himself in Slim’s waiting mouth. Each thrust was nearly concussive, dizzyingly forceful, rattling away his wits until his skull was blissfully empty of everything except the raw physical strain of swallowing Edge down, basking in the taste of his pre-come.

“Good boy,” Black’s warm approval wrapped around him like a blanket, an additional net of safety. He could imagine his brother touching himself, hands down his shorts and delicate fingers dancing numbly between his legs as he pleasured himself to the sight of Edge using his precious dog for their shared enjoyment. 


End file.
